methyl 3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-6-O-picolinyl-α-D-glucopyranosyl)-α-D-glucopyranoside

Base Information

Chemical Name:methyl 3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-6-O-picolinyl-α-D-glucopyranosyl)-α-D-glucopyranoside
CAS No.:1200396-88-8
Molecular Formula:C₆₁H₆₅NO₁₁
Molecular Weight:988.187
Hs Code.:

Synonyms:methyl 3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-6-O-picolinyl-α-D-glucopyranosyl)-α-D-glucopyranoside

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Chemical Property of methyl 3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-6-O-picolinyl-α-D-glucopyranosyl)-α-D-glucopyranoside

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Technology Process of methyl 3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-6-O-picolinyl-α-D-glucopyranosyl)-α-D-glucopyranoside

There total 7 articles about methyl 3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-6-O-picolinyl-α-D-glucopyranosyl)-α-D-glucopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

: 20672-67-7,40246-25-1,40246-30-8,73415-91-5,73445-27-9,81086-90-0,148888-64-6
(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-ol

: phenyl 2,3,4-tri-O-benzyl-6-O-picolinyl-1-thio-β-D-glucopyranoside

: 1200396-88-8
methyl 3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-6-O-picolinyl-α-D-glucopyranosyl)-α-D-glucopyranoside

Guidance literature:: (2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-ol; phenyl 2,3,4-tri-O-benzyl-6-O-picolinyl-1-thio-β-D-glucopyranoside; With palladium(II) bromide; In dichloromethane; at 20 ℃; for 3h; Molecular sieve; Inert atmosphere;

With dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In dichloromethane; at -30 - 20 ℃; for 8h; Inert atmosphere;

With dmap; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;
DOI:10.1021/acs.orglett.5b02110

Reference yield:

: 20672-67-7,40246-25-1,40246-30-8,73415-91-5,73445-27-9,81086-90-0,148888-64-6
(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-ol

: 1200396-62-8
ethyl 2,3,4-tri-O-benzyl-6-O-picolinyl-1-thio-β-D-glucopyranoside

: methyl 3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-6-O-picolinyl-β-D-glucopyranosyl)-α-D-glucopyranoside

: 1200396-88-8
methyl 3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-6-O-picolinyl-α-D-glucopyranosyl)-α-D-glucopyranoside

Guidance literature:: (2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-ol; ethyl 2,3,4-tri-O-benzyl-6-O-picolinyl-1-thio-β-D-glucopyranoside; With palladium(II) bromide; In dichloromethane; at 20 ℃; for 3h; Molecular sieve; Inert atmosphere;

With dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In dichloromethane; at -30 - 20 ℃; for 8h; Inert atmosphere;

With dmap; In dichloromethane; at 20 ℃; for 0.5h; Overall yield = 85 %; Overall yield = 22 mg; Inert atmosphere;
DOI:10.1021/acs.orglett.5b02110

Reference yield:

: 31106-82-8
2-(bromomethyl)pyridine hydrobromide

: 1200396-88-8
methyl 3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-6-O-picolinyl-α-D-glucopyranosyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2.5 h / 20 °C

2.1: palladium(II) bromide / dichloromethane / 3 h / 20 °C / Molecular sieve; Inert atmosphere

2.2: 8 h / -30 - 20 °C / Inert atmosphere

2.3: 0.5 h / 20 °C / Inert atmosphere

With sodium hydride; palladium(II) bromide; In dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/acs.orglett.5b02110